The Deadly Foes of Spider-Man #1 (1991)

Punishment And Crime
"Punishment and Crime" Part 1 of 4. Script by Danny Fingeroth. Pencils Al Milgrom and Kerry Gammill. Inks by Mike Machlan. Cover by Al Milgrom. The Sinister Syndicate is back in business! And their first mission is to rob the Federal Reserve Bank! The Beetle, Boomerang, Hydro-Man, Rhino, and Speed Demon easily knock out the guards and open the vault! However before the quintet of super-villains can escape with the gold, the Spectacular Spider-Man arrives on the scene! The Beetle wisely tells his teammates to ignore the wall-crawler and focus on their getaway! But Boomerang can't resist taking a potshot at the web-slinger! And that foolish action results in Boomerang's capture...and starts the splintering of the syndicate! First appearance of Leila Davis (aka Hardshell). Cameo appearances by the Shocker, Tinkerer, Kingpin, and Pembroke. (Notes: The Sinister Syndicate previously appeared in Amazing Spider-Man 281 & 282. This four-part story was reprinted in 1994 in the trade paperback: Deadly Foes of Spider-Man; and again in 2011 in the trade paperback: Spider-Man: Deadly Foes of Spider-Man. 32 pages. Cover price $1.00.
Release Date: 1991